In agile environments, retrospectives form part of every sprint process and provides an opportunity for teams to reflect on what can be improved to become more effective. In this talk, we will reflect on: security incidents, important vulnerabilities and political events of the past year and highlight important lessons that can be learnt from these events. These events include but are not limited to: the hysteria around GDPR, the lingering effects of the the NotPeyta malware outbreak, the Trustico & UnderArmour incidents, the increasing popularity of security analysis tools to assist cheating in online gaming and the analysis of some interesting traffic picked up by some honeypots. This talk will cover a wide range of topics and will appeal to a broad audience.